| 1. Jornada | 11.08.2023 | Roda JC Kerkrade | - | Helmond Sport | 4:1 | ||||
| 2. Jornada | 18.08.2023 | Helmond Sport | - | FC Den Bosch | 1:0 | ||||
| 3. Jornada | 28.08.2023 | Jong PSV | - | Helmond Sport | 2:1 | ||||
| 4. Jornada | 01.09.2023 | Helmond Sport | - | SC Cambuur | 2:1 | ||||
| 12. Jornada | 27.10.2023 | NAC Breda | - | Helmond Sport | 1:1 |  |
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| 13. Jornada | 03.11.2023 | Helmond Sport | - | Telstar | 1:0 | ||||
| 14. Jornada | 10.11.2023 | AZ Alkmaar (J) | - | Helmond Sport | 2:1 | ||||
| 16. Jornada | 24.11.2023 | Helmond Sport | - | FC Emmen | 1:2 | ||||
| 15. Jornada | 27.11.2023 | Jong Ajax | - | Helmond Sport | 4:1 | ||||
| 17. Jornada | 01.12.2023 | Helmond Sport | - | ADO Den Haag | 3:2 | ||||
| 18. Jornada | 08.12.2023 | Helmond Sport | - | MVV | 1:2 | ||||
| 19. Jornada | 15.12.2023 | Willem II | - | Helmond Sport | 4:1 | ||||
| 20. Jornada | 23.12.2023 | Helmond Sport | - | Roda JC Kerkrade | 3:3 | ||||
| 23. Jornada | 26.01.2024 | Helmond Sport | - | NAC Breda | 1:0 | ||||
| 25. Jornada | 09.02.2024 | Telstar | - | Helmond Sport | 3:2 | ||||
| 34. Jornada | 12.04.2024 | ADO Den Haag | - | Helmond Sport | 0:1 | ||||
| 37. Jornada | 03.05.2024 | Helmond Sport | - | FC Eindhoven | 2:0 |
Países Bajos